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All Caribbean Cruises with Windstar Cruises in December 2027

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  • 2028
October 2026 November 2026 December 2026
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January 2028 February 2028 March 2028
12 cruises
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
Suite External from £2,144
price per person Taxes included
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Wind Surf | 27 Dec 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from £2,154
price per person Taxes included
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Star Legend | 20 Dec 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
Suite External from £2,422
price per person Taxes included
See the cruise Book
Wind Surf | 12 Dec 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from £2,434
price per person Taxes included
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Star Legend | 27 Dec 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. Saint George,
3. Bequia,
4. Mayreau,
5. Les Saintes,
6. Marigot,
7. Saint Johns
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
Suite External from £2,529
price per person Taxes included
See the cruise Book
Wind Surf | 5 Dec 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Sint Maarten, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Virgin Islands, United States
Philipsburg Itinerary Caribbean
Suite External from £2,670
price per person Taxes included
See the cruise Book
Wind Surf | 19 Dec 2027
Duration: 8 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Gustavia,
4. Tortola Island,
5. Tortola Island,
6. Jost Van Dyke,
7. Jost Van Dyke,
8. Virgin Gorda,
9. Charlestown,
10. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
Suite External from £3,315
price per person Taxes included
See the cruise Book
Wind Surf | 27 Dec 2027
Duration: 13 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. Tortola Island,
10. Gustavia,
11. Jost Van Dyke,
12. Virgin Gorda,
13. Tortola Island,
14. Philipsburg
Caribbean: Sint Maarten, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Virgin Islands, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
Suite External from £4,007
price per person Taxes included
See the cruise Book
Wind Surf | 19 Dec 2027
Duration: 15 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Gustavia,
4. Tortola Island,
5. Tortola Island,
6. Jost Van Dyke,
7. Jost Van Dyke,
8. Virgin Gorda,
9. Charlestown,
10. Philipsburg,
11. Charlestown,
12. Roseau,
13. Mayreau,
14. Les Saintes,
15. Basseterre,
16. Gustavia,
17. Philipsburg
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from £4,033
price per person Taxes included
See the cruise Book
Star Legend | 27 Dec 2027
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. Saint George,
3. Bequia,
4. Mayreau,
5. Les Saintes,
6. Marigot,
7. Saint Johns,
8. St. John ,
9. Gustavia,
10. Basseterre,
11. Philipsburg,
12. Jost Van Dyke,
13. Virgin Gorda,
14. Saint Johns
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from £4,033
price per person Taxes included
See the cruise Book
Star Legend | 20 Dec 2027
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns,
9. Saint George,
10. Bequia,
11. Mayreau,
12. Les Saintes,
13. Marigot,
14. Saint Johns
12 cruises